Proline

Proline is an amino acid and belongs to the class which has hydrocarbon R-groups. "It does not contain the amino group -NH2 but is rather a secondary amine. The secondary amine nitrogen is in the protonated NH2+ form under biological conditions, while the carboxy group is in the deprotonated -COO- form. The "side chain" from the alpha-carbon connects to the nitrogen forming a pyrrolidine loop, classifying it as a aliphatic amino acid."

"Proline is the only proteinogenic amino acid which is a secondary amine, in that the nitrogen atom is attached to the alpha-carbon by a chain of three other carbon atoms."

"The distinctive cyclic structure of proline's side chain gives proline an exceptional conformational rigidity compared to other amino acids. It also affects the rate of peptide bond formation between proline and other amino acids. When proline is bound as an amide in a peptide bond, its nitrogen is not bound to any hydrogen, meaning it cannot act as a hydrogen bond donor, but can be a hydrogen bond acceptor."

"The exceptional conformational rigidity of proline affects the secondary structure of proteins near a proline residue and may account for proline's higher prevalence in the proteins of thermophilic organisms. "

"Proline is commonly found as the first residue of an alpha helix and also in the edge strands of beta sheets. Proline is also commonly found in turns (another kind of secondary structure), and aids in the formation of beta turns. "